I've been dressing for practically my whole life and have started on the path to transition.  I have a wife who tries to be accepting but doesn't want to be there when I'm me so I end up with an evening, once a week, in the spare room, alone.

I travel quite a lot through work and my therapist suggested me trying out taking my girl clothes with me when I travel and dressing in my hotel room, maybe advancing to going out where no one would know me.

So here I am. Sat in a hotel room in Chicago as Tammy and it's awesome. I can't believe I've not done this before! Despite being scared about having to place a bag full of liquid eye liner, foundation and mascara on the TSA belt I'm so happy to be sat here now as Tammy.

All this has begged the question. Has anyone experienced going out for the first time in a strange city? How do you do it, order an Uber then slip out of the back door of the hotel?

I tend to travel all over the country.  Are there any 'friendly' hotels in any cities!

Love Tammy x

I suspect hotels have seen most anything with unmarried couples turning the rooms into love nests so being transgender shouldn't be that much out of the norm. Most of the time when I have stayed in rooms, they had direct outside access though I have to admit, that's mostly motels 6 and not the better class of hotels.

I would suggest that you make a scouting trip around the city in male mode before attempting it in Tammy mode. This will give you a little comfort with the area and as long as you don't stop anywhere very long, nobody should remember you. If it's a city you have been to before, you may wish to skip the scouting and go directly to Tammy.